Sciencemadness Discussion Board

Oxidation of amines to nitro by KMnO4

Beanspike - 19-4-2006 at 08:18

I found this reaction in an advanced organic chem book.

R3CNH2 ---(KMnO4)--> R3CNO2

It says that this works best with tertiary alkyl primary amines, but it didn't say a whole lot else.
Does anyone have more information about this, or have done it before? It seems like it would be a really good way to get nitro compounds without having to use Sulfuric or Nitric acids.
I'll be looking into this more as I have time (finals are soon :o ).

Marvin - 20-4-2006 at 01:00

The nitro compounds you make are different from aliphatic nitro compounds made from mixed acid nitrations. Thing is, its not so much an alternative way of making tertiary nitro compounds, as one of the few ways to make them with any kind of yeild at all and you have to make the amine yourself anyway.

I think there is information on these reactions on one of the affiliated FTPs.